Director of AI Strategy

Go Cadre • San Diego, CA

1d

About The Position

The Director of AI Strategy is a senior, AI-first leader who owns end-to-end AI transformation for a portfolio of 5–10 clients. You serve as their fractional Director of AI Strategy—embedded in their organizations as their most senior AI voice—while leading a cross-functional pod of approximately five AI strategists, engineers, and automation specialists.
This is a leadership role with real P&L accountability. You manage the financial performance of your pod, drive client retention and expansion, lead new sales cycles within existing accounts, and ensure your team delivers exceptional results. You need to speak fluently with C-suite executives, translate business problems into technical solutions, and drive measurable impact across complex environments.
There is no hand-off between strategy and execution here. You own both.

Requirements

• 7–10+ years of experience in client-facing businesses or agency environments, with a proven track record of managing multiple client relationships and driving measurable business outcomes
• You have led AI or digital transformation initiatives at scale and can point to specific business results—revenue gained, costs saved, processes eliminated
• Strong people leadership experience: you’ve built, coached, and retained high-performing technical teams, and you know how to develop people without micromanaging them
• P&L accountability is not new to you. You understand how to manage utilization, margin, and revenue growth across a portfolio of accounts
• Deep understanding of AI/ML/LLMs, automation, and applied AI—with the ability to translate complex technical concepts into clear business value for C-suite executives
• Excessively organized. You run multiple complex engagements simultaneously without dropping the ball, and you use tools like ClickUp to keep everything visible and structured
• Exceptional executive presence and communication skills—you’ve run high-stakes client meetings, navigated difficult stakeholder dynamics, and consistently come out as the trusted advisor in the room

Nice To Haves

• You’ve operated as a fractional or embedded strategic leader inside a client organization—not just as an external consultant who shows up with slides
• Track record of expansion: you’ve grown accounts, not just retained them. You can walk into an existing relationship and find the next initiative worth pursuing
• You move fast and stay organized. Ambiguity doesn’t slow you down—you create structure where there isn’t any
• Domain experience in financial services, real estate, private equity, lending, or B2B SaaS
• You’ve led teams that include both strategists and engineers—you know how to bridge those worlds and get the best out of each

Responsibilities

• LEAD AI STRATEGY AND TRANSFORMATION
• Serve as fractional Director of AI Strategy for 5–10 clients, acting as their senior AI leader and strategic advisor
• Define and execute AI roadmaps aligned to business goals, operational realities, competitive dynamics, and measurable ROI
• Lead strategic discovery and planning sessions to identify, prioritize, and scope high-impact AI and automation opportunities across client organizations
• Drive AI transformation across complex organizations, navigating change management, stakeholder alignment, and cross-functional complexity
• Translate complex business problems into technical solutions, bridging the gap between executive vision and engineering execution
• Stay at the forefront of AI innovation—LLMs, agentic AI, automation platforms—to continuously elevate your strategy and recommendations
• OWN CLIENT RELATIONSHIPS AND ACCOUNT GROWTH
• Own the full client relationship as the primary senior point of contact and trusted advisor, building deep executive relationships with C-suite and senior leadership
• Drive client satisfaction, retention, and long-term value creation through consistent delivery of business impact and strategic guidance
• Run client meetings with confidence and precision—executive business reviews, strategy sessions, stakeholder alignment—clearly communicating AI strategy, progress, risks, and outcomes
• Identify and lead expansion opportunities within existing accounts, uncovering new use cases, additional business units, and strategic initiatives that can benefit from AI
• Own the discovery, scoping, proposal, and closing process for expansion opportunities within your portfolio
• LEAD AND DEVELOP YOUR POD
• Lead and develop a cross-functional pod of approximately 5 professionals including AI strategists, engineers, and automation specialists
• Build a high-performing, collaborative team culture focused on excellence, accountability, and continuous improvement
• Manage team performance, coaching, and professional development—providing clear feedback, mentorship, and growth opportunities
• Allocate resources strategically across your client portfolio to maximize utilization, impact, and team satisfaction
• Set clear priorities, expectations, and deliverables for your team across multiple concurrent client engagements
• DRIVE DELIVERY AND EXECUTION
• Oversee end-to-end AI project delivery from discovery and design through implementation, adoption, and optimization
• Ensure projects are delivered on time, within scope, and to the highest quality standards—proactively managing risks and dependencies
• Lead solution design and prototyping, working closely with engineering teams to ensure AI solutions are practical, scalable, and aligned to client needs
• Drive AI adoption and change management, leading or supporting client training, enablement, and organizational adoption initiatives
• Track and report on project progress, delivery performance, and business impact using ClickUp as the core project management system
• OWN P&L AND BUSINESS PERFORMANCE
• Manage the financial performance of your pod: revenue, utilization, margin, and profitability
• Own client retention and revenue growth targets, ensuring your portfolio delivers consistent financial performance
• Drive expansion revenue by identifying, scoping, and closing new opportunities within existing client accounts
• Optimize resource allocation and utilization to balance delivery excellence with financial efficiency
• Participate in performance-based incentives tied to the financial success and growth of your pod

Benefits

• Real ownership. You run your own book of business with full accountability for strategy, delivery, team, and P&L. This is not a support role.
• High-impact work. The AI roadmaps you build and the systems your team ships change how businesses operate. You’ll see the results directly.
• AI-native culture. We don’t just build AI for clients. We use it to run our own operations. You’ll work with people who are as obsessed with the tools as you are.
• Access to the frontier. Through partnerships with Anthropic, OpenAI, and YC, you’ll be among the first to experiment with new models and capabilities.
• Upside. We’re bootstrapped, profitable, and growing fast. Early team members share in the success they help create.
• No bureaucracy. Small pods. Clear accountability. The best idea wins, regardless of who says it.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed